Triethyloxonium tetrafluoroborate → 7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(1,2,4-thiadiazol-5-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1889087
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][NH:17][C:16](=O)[CH2:15]1)=[O:13].F[B-](F)(F)F.C([O+](CC)CC)C.[S:33]1[C:37]([C:38]([NH:40][NH2:41])=O)=[N:36][CH:35]=[N:34]1>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]2[C:38]([C:37]3[S:33][N:34]=[CH:35][N:36]=3)=[N:40][N:41]=[C:16]2[CH2:15]1)=[O:13]

Komponenten

5

Edukt 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 665992084-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-piperazinoneHCID 67970623HCID 67970623, Verbindung

Produkt 1

HCID 665992937-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(1,2,4-thiadiazol-5-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-piperazinone (I1) (0.307 g, 1 mmol) in dry Dichloromethane (DCM) (3 ml) was added triethyloxonium tetrafluoroborate (0.209 g, 1.100 mmol). The solution was then stirred at room temperature and under argon for 30 minutes. 1,2,4-Thiadiazole-5-carbohydrazide (I80) (0.144 g, 1.000 mmol) was then added and the solution was stirred for 1 hour, before the solvent was concentrated and n-BuOH (3.00 ml) was added. The solution was then stirred under argon and reflux for a further 3 hours. The solution was then allowed to cool to room temperature before the solvent was evaporated in vacuo.

Aufarbeitung

  1. stirringthe solution was stirred for 1 hour, before the solvent
  2. concentrationwas concentrated
  3. additionn-BuOH (3.00 ml) was added
  4. stirringThe solution was then stirred under argon
  5. temperaturereflux for a further 3 hours
  6. temperatureto cool to room temperature before the solvent
  7. customwas evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7a9964f64f7d4463a507c1a0c5f79960
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501946B2

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